Ethanone, 2-(2-imidazolidinylidene)-1-phenyl- → 2-(2-Ethoxy-2-phenyl-ethenyl)-2-imidazoline tetrafluoroborate

HRID 1413913Notes

Reaction equation

HRID 1413913 reaction equation
[CH2:1]([O+](CC)CC)[CH3:2].[F:8][B-:9]([F:12])([F:11])[F:10].[NH:13]1[CH2:17][CH2:16][NH:15][C:14]1=[CH:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20]>C(Cl)Cl>[CH2:1]([O:20][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:18][C:14]1[NH:13][CH2:17][CH2:16][N:15]=1)[CH3:2].[F:8][B-:9]([F:12])([F:11])[F:10]

Participants

4

Reactant 2

HCID 821546Ethanone, 2-(2-imidazolidinylidene)-1-phenyl-HCID 2723982Triethyloxonium tetrafluoroborate

Product 1

HCID 867362182-(2-Ethoxy-2-phenyl-ethenyl)-2-imidazoline tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 g (0.105 mole) of triethyloxonium-tetrafluoroborate is dissolved in 200 ml of methylene chloride. To the solution is added 18.8 g (0.1 mole) of crystalline 2-(2--imidazolidinylidene)-acetophenone [m.p. 211°-212°, see J. Klosa, Arch. Pharmaz. 286, 397 (1953)]. After the slightly exothermic reaction has subsided, the reaction mixture, a clear yellow solution, is stirred for 16 hours at room temperature; it is subsequently concentrated to dryness in the rotary evaporator; and the crystallising residue is suspended in 300 ml of ethyl acetate. The suspension is cooled to 5°, and the crystals are filtered off with suction to obtain 2-(2-ethoxy-2-phenyl-ethenyl)-2-imidazoline-tetrafluoroborate, m.p. 151°-152°. After drying at 60° in vacuo, the product is further employed without additional purification.

Workup

  1. customAfter the slightly exothermic reaction
  2. concentrationit is subsequently concentrated to dryness in the rotary evaporator
  3. temperatureThe suspension is cooled to 5°
  4. filtrationthe crystals are filtered off with suction

Sources & evidence

ORD record
ord-a56c90f0bd6d488d91215fc73f661ba4
Source dataset
uspto-grants-1981_02
Patent number
US04251542

Reaction notes

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